4-chloro-1-naphthalenecarboxylic acid

To a solution of 2.44 g (11.9 mmol) of 1-acetyl-4-chloronaphthalene in 5 mL of freshly distilled pyridine under NTo a solution of methyl 4-chloro-1-naphthoate (0.299 g, 1.355 mmol) in methanol (10 ml)-tetrahydrofuran (5 ml) was added 1N aqueous sodium hydroxide solution (2.71 ml, 2.71 mmol), and the mixture was stirred overnight at room temperature. The reaction solution was concentrated, diluted with water, acidified with 1N hydrochloric acid and extracted twice with ethyl acetate. The collected organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was crystallized from diethyl ether-hexane to give the objective substance. pale-brown crystal yield 0.234 g, 84percent mp 215-217°C; 1H-NMR (DMSO-d6, 200MHz) δ 7.74-7.85 (3H, m) , 8.12 (1H, d, J = 7.6 Hz), 8.27 8.35 (1H, m), 8.91-9.00 (1H, m); IR (KBr) 3100-2500, 1690, 1510, 1283, 1252, 785, 762 cm-1; Anal. Calcd for C11H7ClO2*0.2H2O: C, 62.85; H, 3.55. Found: C, 62.99; H, 3.31.(2) 4-Chloro-1-naphthoic acid The compound (8.33 g) obtained in (1) above and a 5% sodium hypochlorite solution (380 ml) were stirred with refluxing for 44 hours. The reaction mixture was cooled to room temperature and concentrated hydrochloric acid (10 ml) was dropwise added. The resulting solid was collected by filtration. The obtained solid was subjected to silica gel column chromatography (hexane-ethyl acetate) to give 1.96 g of a red-brown solid (yield 23%). IR (KBr): 3400, 3000, 2600, 1680, 1565, 1505 cm-1 1 H-NMR (DMSO-d6) delta: 7.72-7.87(3H, m), 8.11(1H, d, J=7.9 Hz), 8.27-8.37(1H, m), 8.90-9.0(1H, m)General procedure: To a solution of 0.07 g (0.44 mmol) of 1-propylindole in 5 mL of dry dichloromethane under Ar was added 0.60 mL (0.60 mmol), of 1 M dimethylaluminum chloride in hexanes and the mixture was stirred for 30 min at 0 C. To this mixture was added dropwise a solution of freshly prepared 4-fluoro-1-naphthoyl chloride in 3 mL of dry dichloromethane. The acid chloride was prepared by the addition of 3 mL (41 mmol) of thionyl chloride to 0.12 g (0.63 mmol) of 4-fluoro-1-naphthoic acid under Ar. The mixture was heated at reflux for 2 h, cooled to ambient temperature and the thionyl chloride was removed in vacuo. The acid chloride was added to the indole mixture without further purification and the mixture was stirred at ambient temperature overnight. The reaction was quenched with water and extracted with ether. The ethereal solution was washed with water and 1 M KOH, dried (MgSO4) and the solvent was removed in vacuo to give the crude product, which was purified by column chromatography (petroleum ether/ether, 8:2) to give 0.076 g (52%) of 1-propyl-3-(4-fluoro-1-naphthoyl)indole as a tan solid

Molecular Weight:206.62
XLogP3:3.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:206.0134572
Monoisotopic Mass:206.0134572
Topological Polar Surface Area:37.3
Heavy Atom Count:14
Complexity:229
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes